Tuning of PCP pincer ligand electronic and steric properties

Topics in Organometallic Chemistry

Volumn 40, Issue , 2013, Pages 49-88

  Roddick, Dean M ^a  

^a UNIVERSITY OF WYOMING   (United States)

Author keywords

Coordination geometries; Electronic effects; Ligand conformation; Phosphine ligands; Pincer ligands; Polydentate ligands; Steric effects; Terdentate ligands

Indexed keywords

EID: 84868595630     PISSN: 14366002     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-3-642-31081-2_3     Document Type: Review

References (187)

1. Choi J, MacArthur AHR, Brookhart M, Goldman AS (2011) Chem Rev 111:1761
2. Albrecht M, van Koten G (2001) Angew Chem Int Ed 40:3750
3. Singleton JT (2003) Tetrahedron 59:1837
4. van der Boom ME, Milstein D (2003) Chem Rev 103:1759
5. Morales-Morales DJ, Craig M (2007) The Chemistry of Pincer Compounds. Elsevier, Amsterdam
6. Benito-Garagorri D, Kirchner K (2008) Acc Chem Res 41:201
7. Morales-Morales D (2008) Mini-Rev Org Chem 5:141
8. Albrecht M, Morales-Morales D, in (2009) Iridium Complexes in Organic Synthesis. Chp. 12, WIley-VCH, p 299
9. Morales-Morales D, in (2009) Iridium Complexes in Organic Synthesis. Chp. 13, WIley-VCH, p 325
10. Serrano-Becerra JM, Morales-Morales D (2009) Curr Org Synth 6:169
11. Leis W, Mayer HA, Kaska WC (2008) Coord Chem Rev 252:1787
12. Gerisch M, Krumper JR, Bergman RG, Tilley TD (2001) J Am Chem Soc 123:5818
13. van Koten G, Grove DM, Van der Zeijden AAH (1989) NATO ASI Ser Ser C 257:477
14. Suijkerbuijk BMJM, Schamhart DJ, Kooijman H, Spek AL, van Koten G, Klein GRJM (2010) Dalton Trans 39:6198
15. Suijkerbuijk BMJM, Tooke DM, Lutz M, Spek AL, Jenneskens LW, van Koten G, Klein GRJM (2010) J Org Chem 75:1534
16. Grove DM, Verschuuren AHM, van Koten G, van Beek JAMJ (1989) J Organomet Chem 372:C1
17. Schimmelpfennig U, Zimmering R, Schleinitz KD, Stoßer R, Wenschuh E, Baumeister U, Hartung H (1993) Zeitschrift fur Anorganische und Allgemeine Chemie 619:1931
18. van Beek JAM, van Koten G, Ramp MJ, Coenjaarts NC, Grove DM, Goubitz K, Zoutberg MC, Stam CH, Smeets WJJ, Spek AL (1991) Inorg Chem 30:3059
19. van de Kuil LA, Grove DM, Gossage RA, Zwikker JW, Jenneskens LW, Drenth W, van Koten G (1997) Organometallics 16:4985
20. Bonnet S, Lutz M, Spek AL, van Koten G, Klein GRJM (2010) Organometallics 29:1157
21. Mehendale NC, Bezemer C, van Walree CA, Klein GRJM, van Koten GJ (2006) Mol Catal A Chem 257:167
22. Mehendale NC, Sietsma JRA, de Jong KP, van Walree CA, Gebbink RJMK, van Koten G (2007) Adv Synth Catal 349:2619
23. Moulton CJ, Shaw BL (1976) J Chem Soc Dalton Trans 1020
24. Bennett MA, Jin H, Willis AC (1993) J Organomet Chem 451:249
25. Creaser CS, Kaska WC (1978) Inorg Chim Acta 30:L325
26. Lu Q, Chen M, Chaloupka S, Venanzi LM (1998) Wuji Huaxue Xuebao 14:449
27. Frech Christian M, Ben-David Y, Weiner L, Milstein D (2006) J Am Chem Soc 128:7128
28. Rybtchinski B, Ben-David Y, Milstein D (1997) Organometallics 16:3786
29. Hollink E, Stewart JC, Wei P, Stephan DW (2003) Dalton Trans 3968
30. Kennedy AR, Cross RJ, Muir KW (1995) Inorg Chim Acta 231:195
31. Punji B, Emge TJ, Goldman AS (2010) Organometallics 29:2702
32. Kundu S, Choliy Y, Zhuo G, Ahuja R, Emge TJ, Warmuth R, Brookhart M, Krogh-Jespersen K, Goldman AS (2009) Organometallics 28:5432
33. Medici S, Gagliardo M, Williams SB, Chase PA, Gladiali S, Lutz M, Spek AL, van Klink GPM, van Koten G (2005) Helv Chim Acta 88:694
34. Morales-Morales D, Cramer RE, Jensen CM (2002) J Organomet Chem 654:44
35. Williams BS, Dani P, Lutz M, Spek AL, van Koten G (2001) Helv Chim Acta 84:3519
36. Longmire JM, Zhang X, Shang M (1998) Organometallics 17:4374
37. Gorla F, Venanzi LM, Albinati A (1994) Organometallics 13:43
38. Gorla F, Togni A, Venanzi LM, Albinati A, Lianza F (1994) Organometallics 13:1607
39. Kozhanov KA, Bubnov MP, Cherkasov VK, Vavilina NN, Efremova LY, Artyushin OI, Odinets IL, Abakumov GA (2008) Dalton Trans 2849
40. Watson WH, Poola B, Liu J, Richmond MG (2007) J Chem Crystallogr 37:349
41. Krogh-Jespersen K, Czerw M, Zhu K, Singh B, Kanzelberger M, Darji N, Achord PD, Renkema KB, Goldman ASJ (2002) Am Chem Soc 124:10797
42. Huang Z, Brookhart M, Goldman AS, Kundu S, Ray A, Scott SL, Vicente BC (2009) Adv Synth Catal 351:188
43. Grimm JC, Nachtigal C, Mack HG, Kaska WC, Mayer HA (2000) Inorg Chem Commun 3:511
44. Mohammad HAY, Grimm JC, Eichele K, Mack H-G, Speiser B, Novak F, Quintanilla MG, Kaska WC, Mayer HA (2002) Organometallics 21:5775
45. Karlen T, Dani P, Grove DM, Steenwinkel P, van Koten G (1996) Organometallics 15:5687
46. Dani P, Karlen T, Gossage RA, Smeets WJJ, Spek AL, van Koten G (1997) J Am Chem Soc 119:11317
47. Beletskaya IP, Chuchurjukin AV, Dijkstra HP, van Klink GPM, van Koten G (2000) Tetrahedron Lett 41:1081
48. Beletskaya IP, Chuchurjukin AV, Dijkstra HP, van Klink GPM, van Koten G (2000) Tetrahedron Lett 41:1075
49. Dani P, Richter B, van Klink GPM, van Koten G (2001) Eur J Inorg Chem 125
50. Sommer WJ, Yu K, Sears JS, Ji Y, Zheng X, Davis RJ, Sherrill CD, Jones CW, Weck M (2005) Organometallics 24:4351
51. Ashkenazi N, Vigalok A, Parthiban S, Ben-David Y, Shimon LJW, Martin JML, Milstein D (2000) J Am Chem Soc 122:8797
52. Kossoy E, Iron Mark A, Rybtchinski B, Ben-David Y, Shimon Linda JW, Konstantinovski L, Martin Jan ML, Milstein D (2005) Chem Eur J 11:2319
53. Chase PA, Gagliardo M, Lutz M, Spek AL, van Klink GPM, van Koten G (2005) Organometallics 24:2016
54. Gagliardo M, Chase PA, Brouwer S, van Klink GPM, van Koten G (2007) Organometallics 26:2219
55. Adams JJ, Lau A, Arulsamy N, Roddick DM (2007) Inorg Chem 46:11328
56. Taylor SD, Dinaut AN, Thadani AN, Huang Z (1996) Tetrahedron Lett 37:8089
57. Taylor SD, Kotoris CC, Dinaut AN, Chen M-J (1998) Tetrahedron 54:1691
58. Caplan NA, Pogson CI, Hayes DJ, Blackburn GM (2000) Perkin 1:421
59. Adams JJ, Lau A, Arulsamy N, Roddick DM (2011) Organometallics 30:689
60. Vigalok A, Uzan O, Shimon LJW, Ben-David Y, Martin JML, Milstein D (1998) J Am Chem Soc 120:12539
61. Gusev DG, Madott M, Dolgushin FM, Lyssenko KA, Antipin MY (2000) Organometallics 19:1734
62. Kozhanov KA, Bubnov MP, Cherkasov VK, Fukin GK, Abakumov GA (2004) Dalton Trans 2957
63. Benito-Garagorri D, Bocokic V, Mereiter K, Kirchner K (2006) Organometallics 25:3817
64. Wallner OA, Olsson VJ, Eriksson L, Szabo KJ (2006) Inorg Chim Acta 359:1767
65. Li J, Lutz M, Spek AL, van Klink GPM, van Koten G, Klein GRJM (2010) Organometallics 29:1379
66. Niu J-L, Chen Q-T, Hao X-Q, Zhao Q-X, Gong J-F, Song M-P (2010) Organometallics 29:2148
67. Gozin M, Weisman A, Ben-David Y, Milstein D (1993) Nature 364:699
68. van der Boom ME, Kraatz H-B, Ben-David Y, Milstein D (1996) Chem Commun 2167
69. van der Boom ME, Kraatz H-B, Hassner L, Ben-David Y, Milstein D (1999) Organometallics 18:3873
70. Gauvin RM, Rozenberg H, Shimon LJW, Milstein D (2001) Organometallics 20:1719
71. van der Boom ME, Liou S-Y, Shimon LJW, Ben-David Y, Milstein D (2004) Inorg Chim Acta 357:4015
72. Salem H, Ben-David Y, Shimon LJW, Milstein D (2006) Organometallics 25:2292
73. Goettker-Schnetmann I, White P, Brookhart M (2004) J Am Chem Soc 126:1804
74. Morales-Morales D, Grause C, Kasaoka K, Redon R, Cramer RE, Jensen CM (2000) Inorg Chim Acta 300-302:958
75. Bedford RB, Draper SM, Noelle SP, Welch SL (2000) New J Chem 24:745
76. Gomez-Benitez V, Baldovino-Pantaleon O, Herrera-Alvarez C, Toscano RA, Morales-Morales D (2006) Tetrahedron Lett 47:5059
77. Ceron-Camacho R, Gomez-Benitez V, Le LR, Morales-Morales D, Toscano RAJ (2006) Mol Catal A Chem 247:124
78. Wallner OA, Szabo KJ (2004) Org Lett 6:1829
79. Hunks WJ, Jennings MC, Puddephatt RJ (2000) Inorg Chem 39:2699
80. Huang Z, White PS, Brookhart M (2010) Nature 465:598
81. Li J, Lutz M, Spek AL, van Klink GPM, van Koten G, Klein GRJM (2010) J Organomet Chem 695:2618
82. Feng J-J, Chen X-F, Shi M, Duan W-L (2010) J Am Chem Soc 132:5562
83. Aydin J, Ryden A, Szabo KJ (2008) Tetrahedron-Asymmetr 19:1867
84. Aydin J, Conrad CS, Szabo KJ (2008) Org Lett 10:5175
85. Rubio M, Suarez A, del RD, Galindo A, Alvarez E, Pizzano A (2007) Dalton Trans 407
86. Aydin J, Kumar KS, Sayah MJ, Wallner OA, Szabo KJ (2007) J Org Chem 72:4689
87. Ini S, Oliver AG, Tilley TD, Bergman RG (2001) Organometallics 20:3839
88. Baber RA, Bedford RB, Betham M, Blake ME, Coles SJ, Haddow MF, Hursthouse MB, Orpen AG, Pilarski LT, Pringle PG, Wingad RL (2006) Chem Commun 3880
89. Balakrishna MS, Kumar P, Punji B, Mague JTJ (2010) Organomet Chem 695:981
90. Sokolov VI, Bulygina LA (2004) Russ Chem Bull 53:2355
91. Miyazaki F, Yamaguchi K, Shibasaki M (1999) Tetrahedron Lett 40:7379
92. Nifantyev EE, Rasadkina EN, Vasyanina LK, Belsky VK, Stash AIJ (1997) Organomet Chem 529:171
93. Bolliger JL, Blacque O, Frech CM (2007) Angew Chem Int Ed 46:6514
94. Bedford RB, Betham M, Charmant JPH, Haddow MF, Orpen AG, Pilarski LT, Coles SJ, Hursthouse MB (2007) Organometallics 26:6346
95. Bell GA, Rankin DWH, Reinisch PFJ (1987) Chem Soc Dalton Trans 3023
96. Ozerov OV, Guo C, Foxman BMJ (2006) Organomet Chem 691:4802
97. Frech CM, Shimon LJW, Milstein D (2005) Angew Chem Int Ed 44:1709
98. Bolliger JL, Frech CM (2009) Adv Synth Catal 351:891
99. Nelson SM, Dahlhoff WV (1971) J Chem Soc A 2184
100. Muller G, Klinga M, Leskela M, Rieger BZ (2002) Anorg Allg Chem 628:2839
101. Hermann D, Gandelman M, Rozenberg H, Shimon LJW, Milstein D (2002) Organometallics 21:812
102. Pelczar EM, Emge TJ, Krogh-Jespersen K, Goldman AS (2008) Organometallics 27:5759
103. Jansen A, Pitter S (1999) Monatsh Chem 130:783
104. Kawatsura M, Hartwig JF (2001) Organometallics 20:1960
105. Yano T, Moroe Y, Yamashita M, Nozaki K (2008) Chem Lett 37:1300
106. Zhang J, Leitus G, Ben-David Y, Milstein D (2005) J Am Chem Soc 127:10840
107. Ben-Ari E, Leitus G, Shimon LJW, Milstein D (2006) J Am Chem Soc 128:15390
108. Zhang J, Leitus G, Ben-David Y, Milstein D (2006) Angew Chem Int Ed 45:1113
109. Bernskoetter WH, Hanson SK, Buzak SK, Davis Z, White PS, Swartz R, Goldberg KI, Brookhart M (2009) J Am Chem Soc 131:8603
110. Bernskoetter WH, Schauer CK, Goldberg KI, Brookhart M (2009) Science 326:553
111. Salem H, Shimon LJW, Diskin-Posner Y, Leitus G, Ben-David Y, Milstein D (2009) Organometallics 28:4791
112. Schirmer W, Floerke U, Haupt HJZ (1987) Anorg Allg Chem 545:83
113. Benito-Garagorri D, Wiedermann J, Pollak M, Mereiter K, Kirchner K (2007) Organometallics 26:217
114. Tolman CA (1977) Chem Rev 77:313
115. Brown TL, Lee KJ (1993) Coord Chem Rev 128:89
116. Bunten KA, Chen L, Fernandez AL, Poe AJ (2002) Coord Chem Rev 233-234:41
117. Dunne BJ, Morris RB, Orpen AG (1991) J Chem Soc Dalton Trans 653
118. Brown TL (1992) Inorg Chem 31:1286
119. White D, Coville NJ (1994) Adv Organomet Chem 36:95
120. Albert P, Biagio C, Andrea C, Simona G, Francesco R, Vittorio S, Luigi C (2009) Eur J Inorg Chem 2009:1759
121. Clavier H, Nolan SP (2010) Chem Commun 46:841
122. Poverenov E, Leitus G, Shimon LJW, Milstein D (2005) Organometallics 24:5937
123. Frech CM, Shimon LJW, Milstein D (2009) Organometallics 28:1900
124. Kimmich BFM, Marshall WJ, Fagan PJ, Hauptman E, Bullock RM (2002) Inorg Chim Acta 330:52
125. Kanzelberger M, Zhang X, Emge TJ, Goldman AS, Zhao J, Incarvito C, Hartwig JF (2003) J Am Chem Soc 125:13644
126. van der Boom ME, Iron MA, Atasoylu O, Shimon LJW, Rozenberg H, Ben-David Y, Konstantinovski L, Martin JML, Milstein D (2004) Inorg Chim Acta 357:1854
127. Ghosh R, Emge TJ, Krogh-Jespersen K, Goldman AS (2008) J Am Chem Soc 130:11317
128. Steffey BD, Miedaner A, Maciejewski-Farmer ML, Bernatis PR, Herring AM, Allured VS, Carperos V, DuBois DL (1994) Organometallics 13:4844
129. Gagliardo M, Dijkstra HP, Coppo P, De CL, Lutz M, Spek AL, van Klink GPM, van Koten G (2004) Organometallics 23:5833
130. Cross RJ, Kennedy AR, Muir KWJ (1995) J Organomet Chem 487:227
131. Kennedy AR, Cross RJ, Muir KW (1995) Inorg Chim Acta 231:207
132. Kossoy E, Iron MA, Rybtchinski B, Ben-David Y, Shimon LJW, Konstantinovski L, Martin JML, Milstein D (2005) Chem Eur J 11:2319
133. Kossoy E, Rybtchinski B, Diskin-Posner Y, Shimon LJW, Leitus G, Milstein D (2009) Organometallics 28:523
134. Bergbreiter DE, Frels JD, Rawson J, Li J, Reibenspies JH (2006) Inorg Chim Acta 359:1912
135. Tuba RT, Verona, Dinh Long V, Hampel Frank, Gladysz John A (2005) J Chem Soc Dalton Trans 2275
136. Naghipour A, Sabounchei SJ, Morales-Morales D, Hernandez-Ortega S, Jensen CM (2004) J Organomet Chem 689:2494
137. Adams JJ, Arulsamy N, Roddick DM (2011) Organometallics 30:697
138. Liou S-Y, Gozin M, Milstein D (1995) J Am Chem Soc 117:9774
139. Kuklin SA, Sheloumov AM, Dolgushin FM, Ezernitskaya MG, Peregudov AS, Petrovskii PV, Koridze AA (2006) Organometallics 25:5466
140. Cartwright SA, White P, Brookhart M (2006) Organometallics 25:1664
141. Polezhaev AV, Kuklin SA, Ivanov DM, Petrovskii PV, Dolgushin FM, Ezernitskaya MG, Koridze AA (2009) Russ Chem Bull 58:1847
142. Kimura T, Uozumi Y (2006) Organometallics 25:4883
143. Rubio M, Suarez A, Del RD, Galindo A, Alvarez E, Pizzano A (2009) Organometallics 28:547
144. Lang H-F, Fanwick PE, Walton RA (2002) Inorg Chim Acta 329:1
145. Katayama H, Wada C, Taniguchi K, Ozawa F (2002) Organometallics 21:3285
146. Melaimi M, Thoumazet C, Ricard L, Floch PLJ (2004) Organomet Chem 689:2988
147. Wiedermann J, Benito-Garagorri D, Kirchner K, Mereiter K (2006) Acta Crystallogr Sect E Struct Rep Online E62:m1106
148. Benito-Garagorri D, Becker E, Wiedermann J, Lackner W, Pollak M, Mereiter K, Kisala J, Kirchner K (2006) Organometallics 25:1900
149. Gaviglio C, Ben-David Y, Shimon LJW, Doctorovich F, Milstein D (2009) Organometallics 28:1917
150. Feller M, Ben-Ari E, Gupta T, Shimon LJW, Leitus G, Diskin-Posner Y, Weiner L, Milstein D (2007) Inorg Chem 46:10479
151. Feller M, Iron MA, Shimon LJW, Diskin-Posner Y, Leitus G, Milstein D (2008) J Am Chem Soc 130:14374
152. Salem H, Shimon LJW, Leitus G, Weiner L, Milstein D (2008) Organometallics 27:2293
153. Sykes AC, White P, Brookhart M (2006) Organometallics 25:1664
154. Ben-Ari E, Gandelman M, Rozenberg H, Shimon LJW, Milstein D (2003) J Am Chem Soc 125:4714
155. Ben-Ari E, Cohen R, Gandelman M, Shimon LJW, Martin JML, Milstein D (2006) Organometallics 25:3190
156. Ghosh R, Zhang X, Achord P, Emge TJ, Krogh-Jespersen K, Goldman AS (2007) J Am Chem Soc 129:853
157. Gusev DG, Dolgushin FM, Antipin MY (2001) Organometallics 20:1001
158. Amoroso D, Jabri A, Yap GPA, Gusev DG, dos Santos EN, Fogg DE (2004) Organometallics 23:4047
159. Gagliardo M, Chase PA, Lutz M, Spek AL, Hartl F, Havenith RWA, van Klink GPM, van Koten G (2005) Organometallics 24:4553
160. Wen TB, Cheung YK, Yao J, Wong W-T, Zhou ZY, Jia G (2000) Organometallics 19:3803
161. Zhang J, Gandelman M, Herrman D, Leitus G, Shimon LJW, Ben-David Y, Milstein D (2006) Inorg Chim Acta 359:1955
162. Benito-Garagorri D, Puchberger M, Mereiter K, Kirchner K (2008) Angew Chem Int Ed 47:9142
163. Trovitch RJ, Lobkovsky E, Chirik PJ (2006) Inorg Chem 45:7252
164. Lian Zhe, Xu G, Li Xiaoyan (2010) Acta Crystallogr Sect E Struct Rep Online 66:m636
165. Wen TB, Zhou ZY, Jia G (2006) Angew Chem Int Ed 45:5842
166. Liu F, Goldman AS (1999) Chem Commun 655
167. Huang K-W, Grills DC, Han JH, Szalda DJ, Fujita E (2008) Inorg Chim Acta 361:3327
168. Figgen D, Peterson KA, Dolg M, Stoll H (2009) J Chem Phys 130:164108/1
169. Gerber R, Fox T, Frech CM (2010) Chem Eur J 16:6771
170. Bolliger JL, Blacque O, Frech CM (2008) Chem Eur J 14:7969
171. Vuzman D, Poverenov E, Diskin-Posner Y, Leitus G, Shimon LJW, Milstein D (2007) Dalton Trans 5692
172. Goettker-Schnetmann I, White PS, Brookhart M (2004) Organometallics 23:1766
173. Kloek SM, Heinekey DM, Goldberg KI (2006) Organometallics 25:3007
174. Hansch C, Leo A, Taft RW (1991) Chem Rev 91:165
175. Perrin L, Clot E, Eisenstein O, Loch J, Crabtree RH (2001) Inorg Chem 40:5806
176. Zhu K, Achord PD, Zhang X, Krogh-Jespersen K, Goldman AS (2004) J Am Chem Soc 126:13044
177. Novak F, Speiser B, Mohammad HAY, Mayer HA (2004) Electrochim Acta 49:3841
178. Merwin RK, Ontko AC, Houlis JF, Roddick DM (2004) Polyhedron 23:2873
179. Ontko AC, Houlis JF, Schnabel RC, Roddick DM, Fong TP, Lough AJ, Morris RH (1998) Organometallics 17:5467
180. Ernst MF, Roddick DM (1990) Organometallics 9:1586
181. Castonguay A, Beauchamp AL, Zargarian D (2008) Organometallics 27:5723
182. Castonguay A, Spasyuk DM, Madern N, Beauchamp AL, Zargarian D (2009) Organometallics 28:2134
183. Gagliardo M, Havenith RWA, van Klink G, van Koten GJ (2006) Organomet Chem 691:4411
184. Goettker-Schnetmann I, Brookhart M (2004) J Am Chem Soc 126:9330
185. Zhao J, Goldman AS, Hartwig JF (2005) Science 307:1080
186. Bursten BE, Chen S, Chisholm MH (2008) J Organomet Chem 693:1547
187. Gruver BC, Adams JJ, Warner SJ, Arulsamy N, Roddick DM (2011) Organometallics 30:5133